Cabotegravir

Cabotegravir
Clinical data
Trade names	Vocabria, Apretude
Other names	S/GSK1265744, GSK744
AHFS/Drugs.com	Monograph
MedlinePlus	a621010
License data	US DailyMed: Cabotegravir;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth, intramuscular
ATC code	J05AJ04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	>99%
Metabolism	UGT1A1
Metabolites	glucuronide
Elimination half-life	tablets: 41 hours; injection: 5.6–11.5 weeks
Excretion	47% via feces, 27% via urine
Identifiers
	IUPAC name N-((2,4-Difluorophenyl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide;
CAS Number	1051375-10-0 ; as salt: 1051375-13-3;
PubChem CID	54713659; as salt: 46215800;
DrugBank	DB11751; as salt: DBSALT002064;
ChemSpider	30829503; as salt: 32702138;
UNII	HMH0132Z1Q; as salt: 3L12PT535M;
KEGG	D10548; as salt: D10549;
ChEBI	CHEBI:172944; as salt: CHEBI:172948;
ChEMBL	ChEMBL2403238 ; as salt: ChEMBL3137330;
CompTox Dashboard (EPA)	DTXSID50146982 ;
ECHA InfoCard	100.306.452
Chemical and physical data
Formula	C19H17F2N3O5
Molar mass	405.358 g·mol−1
3D model (JSmol)	Interactive image; as salt: Interactive image;
	SMILES C[C@H]1CO[C@H]2N1C(=O)c3c(c(=O)c(cn3C2)C(=O)NCc4ccc(cc4F)F)O; ; as salt: [Na+].C[C@H]1CO[C@@H]2CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C([O-])=C3C(=O)N12;
	InChI InChI=1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1; Key:WCWSTNLSLKSJPK-LKFCYVNXSA-N; ; as salt: InChI=1S/C19H17F2N3O5.Na/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21;/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27);/q;+1/p-1/t9-,14+;/m0./s1; Key:AEZBWGMXBKPGFP-KIUAEZIZSA-M;

Cabotegravir, sold under the brand name Vocabria among others, is an antiretroviral medication used for the treatment and prevention of HIV/AIDS. It is available in the form of tablets and as an intramuscular injection, as well as in an injectable combination with rilpivirine under the brand name Cabenuva.

It is an integrase inhibitor with a carbamoyl pyridone structure similar to that of dolutegravir.

In December 2021, the U.S. Food and Drug Administration approved cabotegravir for pre-exposure prophylaxis (PrEP) in at-risk people under the brand name Apretude. In September 2023, it was approved for pre-exposure prophylaxis in the European Union.